4-tert-Butylphthalic anhydride → HCID 15543027, compound

HRID 842377Notes

Reaction equation

HRID 842377 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[N:12][N:13]2C(OC(C)(C)C)=O)=[CH:9][CH:8]=1)=[O:5].[C:27]([C:31]1[CH:32]=[C:33]2[C:38](=O)[O:37][C:35](=[O:36])[C:34]2=[CH:40][CH:41]=1)([CH3:30])([CH3:29])[CH3:28]>C1COCC1.C(OCC)C>[NH:13]1[C:14]2[C:10](=[CH:9][CH:8]=[C:7]([NH:6][C:4](=[O:5])[C:3]3[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=3[N:1]3[C:38](=[O:37])[C:33]4[C:34](=[CH:40][CH:41]=[C:31]([C:27]([CH3:29])([CH3:28])[CH3:30])[CH:32]=4)[C:35]3=[O:36])[CH:15]=2)[CH:11]=[N:12]1

Participants

5

Reactant 2

HCID 1229304-tert-Butylphthalic anhydrideHCID 15543039HCID 15543039, compound

Product 1

HCID 15543027HCID 15543027, compoundYield 16.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2-amino-N-(1-Boc-6-indazolyl)benzamide (1 g, 2.8 mmol) in THF (30 mL) was added 4-t-butylphthalic anhydride (1.2 g, 5.9 mmol) and the solution was heated to reflux. After 72 h, the vessel was cooled and the volume was reduced to about 10 mL in vacuo. The mixture was diluted with diethyl ether (20 mL) and after sonication, a white solid was collected. This solid was processed by methods substatially equivalent to those described in Example 2-F to give 200 mg of N-(6-indazolyl)-2-(5-t-butyl-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)benzamide.

Workup

  1. temperaturethe solution was heated to reflux
  2. temperaturethe vessel was cooled
  3. customafter sonication
  4. customa white solid was collected

Sources & evidence

ORD record
ord-2c4326fb26734b81a52ffccf4ebd45c4
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

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